(R)-(−)-Aloesaponol III 8-Methyl Ether from Eremurus persicus: A Novel Compound against Leishmaniosis

Abstract

Leishmaniosis is a neglected tropical disease which affects several millions of people worldwide. The current drug therapies are expensive and often lack efficacy, mainly due to the development of parasite resistance. Hence, there is an urgent need for new drugs effective against Leishmania infections. As a part of our ongoing study on the phytochemical characterization and biological investigation of plants used in the traditional medicine of western and central Asia, in the present study, we focused on Eremurus persicus root extract in order to evaluate its potential in the treatment of leishmaniosis. As a result of our study, aloesaponol III 8-methyl ether (ASME) was isolated for the first time from Eremurus persicus root extract, its chemical structure elucidated by means of IR and NMR experiments and the (R) configuration assigned by optical activity measurements: chiroptical aspects were investigated with vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) spectroscopies and DFT (density functional theory) quantum mechanical calculations. Concerning biological investigations, our results clearly proved that (R)-ASME inhibits Leishmania infantum promastigotes viability (IC50 73 µg/mL), inducing morphological alterations and mitochondrial potential deregulation. Moreover, it is not toxic on macrophages at the concentration tested, thus representing a promising molecule against Leishmania infections.

Marrubium vulgare L. Leave Extract: Phytochemical Composition, Antioxidant and Wound Healing Properties

“…According to the data reported in literature, the air-dried leaves of Marrubium vulgare L. were extracted with a solution of 80/20 methanol (MeOH)/water ( v / v ) [ 24 ]. Basing on our experience in this field [ 33 , 34 , 35 , 36 , 37 ], we set up a microwave-assisted solvent extraction (MASE) procedure. Briefly, the plant material was extracted with a 80/20 MeOH/water solution ( v / v ) in a multimode (for processing bulk materials) microwave apparatus at 60 °C for 10 min with a power of 800 W. The extract was separated by Buchner filtration, the so-obtained crude extract was treated with charcoal to remove the chlorophyll and then with polivinylpirrolidone (PVP) to take out tannins, which can alter the results of biological assays [ 38 ].…”

“…Considering that phenols and related compounds may improve the proliferation of fibroblasts and the migration of cells, thus promoting the formation of new blood vessels and capillaries [ 25 , 32 ], in the present study we focus our attention on Marrubium vulgare L. leaves. Based on our experience, we prepared a hydroalcoholic leave extract (HA-LE) applying a Microwave Assisted Solvent Extraction (MASE), a methodology suitable for preparing high-values bioactive extracts [ 33 , 34 , 35 ]. The content of phenols and flavonoids was evaluated via colorimetric analysis and the amount of marrubiin determined by quantitative Nuclear Magnetic Resonance (q-NMR).…”

Phytotoxic Activity of Metabolites Isolated from Rutstroemia sp.n., the Causal Agent of Bleach Blonde Syndrome on Cheatgrass (Bromus tectorum)

“…The similarity factors [ 21 , 22 ] were estimated as 0.57 for ( R ) enantiomer and 0.037 for the ( S ) enantiomers by VCD. The use of two chiroptical techniques, whose conclusions reinforce each other, is especially important when dealing with weak ECD or VCD spectra, as in the current and similar cases [ 30 , 31 ]. Thus, the absolute configuration of 9- O -methylfusarubin is assigned as ( R )- 1 .…”

Intra- and interspecific diversity analyses in the genus Eremurus in Iran using genotyping-by-sequencing reveal geographic population structure

“…Due to their large and colorful floral spikes, Eremurus species are known in the international horticulture trade as "Foxtail Lily" or "Desert Candle". In addition to their ornamental value, Eremurus species have been used in traditional medicine and are potential sources for anti-inflammatory, antibacterial, and antiprotozoal drugs [3][4][5] . Other Eremurus products, such as bio-oil 6 and adhesives 7 , have industrial applications.…”